catena-Poly[[[aqua­silver(I)]-μ-1,1′-(butane-1,4-di­yl)di-1H-imidazole-κ2N3:N3′] hemi(biphenyl-4,4′-dicarboxyl­ate) dihydrate]

Zhang, Z.

doi:10.1107/S1600536809045826

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1519-m1520

doi:10.1107/S1600536809045826

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catena-Poly[[[aquasilver(I)]-μ-1,1′-(butane-1,4-diyl)di-1H-imidazole-κ²N³:N^3′] hemi(biphenyl-4,4′-dicarboxylate) dihydrate]

Zheyu Zhang ^a ^*

^aDepartment of Chemistry, Baicheng Normal College, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: chemzyzhang@yahoo.cn

(Received 13 October 2009; accepted 1 November 2009; online 7 November 2009)

In the title compound, {[Ag(C₁₀H₁₄N₄)(H₂O)](C₁₄H₈O₄)_0.5·2H₂O}_n, the Ag^I ion is three-coordinated by two N atoms from two independent 1,1′-(butane-1,4-diyl)di-1H-imidazole (BBI) ligands and one water O atom in a distorted T-shaped coordination geometry. The biphenyl-4,4′-dicarboxylate (BPDC) dianions do not coordinate to Ag^I ions but act as counter-ions. The Ag^I ions are linked by BBI ligands, forming a zigzag chain. These chains are linked into a two-dimensional supramolecular architecture by O—H⋯O hydrogen-bonding interactions between water molecules and carboxylate O atoms of the BPDC dianions.

Related literature

For general background to the design and construction of metal-organic frameworks, see: Kitagawa et al. (2004 ); Ma et al. (2009 ); Li et al. (2005 ). For a related structure, see: Ma et al. (2005 ).

Experimental

Crystal data

[Ag(C₁₀H₁₄N₄)(H₂O)](C₁₄H₈O₄)_0.5·2H₂O
M_r = 472.27
Triclinic, $[P \overline 1]$
a = 9.7685 (6) Å
b = 10.0659 (6) Å
c = 10.9224 (7) Å
α = 80.190 (1)°
β = 68.898 (1)°
γ = 74.775 (1)°
V = 963.36 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 293 K
0.23 × 0.16 × 0.14 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.81, T_max = 0.86
5289 measured reflections
3569 independent reflections
3422 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.058
S = 1.06
3569 reflections
267 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.1209 (17)
Ag1—O1W	2.6611 (12)
Ag1—N3	2.1237 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2A⋯O1ⁱ	0.86 (2)	1.99 (2)	2.833 (2)	166 (3)
O2W—H2B⋯O1ⁱⁱ	0.84 (2)	1.95 (2)	2.779 (2)	169 (3)
O3W—H3B⋯O1ⁱⁱⁱ	0.86 (2)	2.05 (2)	2.877 (2)	160 (2)
O3W—H3A⋯O1W	0.86 (2)	2.02 (2)	2.852 (2)	161 (2)
O1W—H1A⋯O2W^iv	0.84 (2)	2.03 (2)	2.802 (2)	153 (2)
Symmetry codes: (i) x, y+1, z-1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x+1, y-1, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045826/ci2938sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045826/ci2938Isup2.hkl

checkCIF report

Comment top

Design of effective ligands and the proper choice of metal centers are the keys to design and construct novel metal-organic frameworks (Kitagawa et al., 2004; Ma et al., 2009). These complexes can be specially designed by careful selection of metal cations with preferred coordination geometries, nature of the anions, structures of connecting ligands, and the reaction conditions (Li et al., 2005). In this contribution, we selected biphenyl-4,4'-dicarboxylic acid (H₂BPDC) as an organic carboxylate anion and 1,1'-(butane-1,4-diyl)di-1H-imidazole (BBI) as a N-donor neutral ligand, generating a coordination compound, [Ag(BPDC)_0.5(H₂O)(BBI)].2H₂O, which is reported here.

In the title compound, each Ag^I ion is three-coordinated by two N atoms from two independent half-units of the BBI ligands and one water molecule in a distorted T-shaped coordination geometry. The Ag—N and Ag—O distances are comparable to those found in other crystallographically characterized Ag^I complexes (Ma et al., 2005). The adjacent Ag^I ions are linked by BBI ligands to give a one-dimensional zigzag chain. Biphenyl-4,4'-dicarboxylate anions, acting as counterions, have no contribution to the formation of the final structure (Fig. 1). However, there are intermolecular O—H···O hydrogen bonding interactions among water molecules and BPDC anions. These hydrogen bonds extend zigzag chains into a two-dimensional supramolecular architecture.

Related literature top

For general background to the design and construction of metal-organic frameworks, see: Kitagawa et al. (2004); Ma et al. (2009); Li et al. (2005). For a related structure, see: Ma et al. (2005).

Experimental top

To a mixture of biphenyl-4,4'-dicarboxylic acid (0.0484 g, 0.2 mmol) and Ag₂CO₃ (0.0275 g, 0.1 mmol) in water was added 1,1'-(butane-1,4-diyl)di-1H-imidazole (0.2 mmol, 0.038 g) with constant stirring. After the sample was stirred for 10 min, the precipitate was dissolved by dropwise addition of aqueous NH₃ solution. Colourless crystals were obtained from the filtrate by slow evaporation after standing in the dark for several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Constituent units of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 3 - x, 1 - y, -z; (iii) 1 - x, -y, 2 - z.

catena-Poly[[[aquasilver(I)]-µ-1,1'-(butane-1,4-diyl)di-1H- imidazole-κ²N³:N^3'] hemi(biphenyl-4,4'-dicarboxylate) dihydrate] top

Crystal data top

[Ag(C₁₀H₁₄N₄)(H₂O)](C₁₄H₈O₄)_0.5·2H₂O	Z = 2
M_r = 472.27	F(000) = 482
Triclinic, P1	D_x = 1.628 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7685 (6) Å	Cell parameters from 3658 reflections
b = 10.0659 (6) Å	θ = 2.0–25.7°
c = 10.9224 (7) Å	µ = 1.08 mm⁻¹
α = 80.190 (1)°	T = 293 K
β = 68.898 (1)°	Block, colourless
γ = 74.775 (1)°	0.23 × 0.16 × 0.14 mm
V = 963.36 (10) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	3569 independent reflections
Radiation source: fine-focus sealed tube	3422 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ϕ and ω scans	θ_max = 25.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.81, T_max = 0.86	k = −12→11
5289 measured reflections	l = −12→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0296P)² + 0.5838P] where P = (F_o² + 2F_c²)/3
3569 reflections	(Δ/σ)_max = 0.003
267 parameters	Δρ_max = 0.36 e Å⁻³
9 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ag(C₁₀H₁₄N₄)(H₂O)](C₁₄H₈O₄)_0.5·2H₂O	γ = 74.775 (1)°
M_r = 472.27	V = 963.36 (10) Å³
Triclinic, P1	Z = 2
a = 9.7685 (6) Å	Mo Kα radiation
b = 10.0659 (6) Å	µ = 1.08 mm⁻¹
c = 10.9224 (7) Å	T = 293 K
α = 80.190 (1)°	0.23 × 0.16 × 0.14 mm
β = 68.898 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3569 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3422 reflections with I > 2σ(I)
T_min = 0.81, T_max = 0.86	R_int = 0.011
5289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	9 restraints
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
3569 reflections	Δρ_min = −0.42 e Å⁻³
267 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.956725 (17)	0.248290 (16)	0.414393 (15)	0.03644 (7)
C1	1.1776 (2)	0.4373 (2)	0.3910 (2)	0.0390 (5)
H1	1.1738	0.4140	0.4781	0.047*
C2	1.2573 (2)	0.5253 (2)	0.3053 (2)	0.0390 (5)
H2	1.3174	0.5731	0.3219	0.047*
C3	1.1389 (2)	0.4463 (2)	0.2074 (2)	0.0325 (4)
H3	1.1042	0.4315	0.1431	0.039*
C4	1.2955 (2)	0.6107 (2)	0.0650 (2)	0.0372 (5)
H4A	1.2605	0.7083	0.0785	0.045*	0.855 (8)
H4B	1.2593	0.5933	−0.0014	0.045*	0.855 (8)
H4C	1.3203	0.6896	0.0832	0.045*	0.145 (8)
H4D	1.2221	0.6428	0.0209	0.045*	0.145 (8)
C5	1.4677 (3)	0.5751 (3)	0.0147 (3)	0.0374 (9)	0.855 (8)
H5A	1.5036	0.6338	−0.0647	0.045*	0.855 (8)
H5B	1.5038	0.5942	0.0804	0.045*	0.855 (8)
C5A	1.4372 (14)	0.5180 (14)	−0.0276 (12)	0.024 (4)*	0.145 (8)
H5C	1.4122	0.4341	−0.0372	0.029*	0.145 (8)
H5D	1.4686	0.5669	−0.1141	0.029*	0.145 (8)
C6	0.5360 (2)	0.0327 (2)	0.93096 (18)	0.0289 (4)
H6A	0.4580	0.0804	0.8937	0.035*
H6B	0.5876	0.1004	0.9370	0.035*
C7	0.6471 (2)	−0.0754 (2)	0.84084 (19)	0.0305 (4)
H7A	0.7307	−0.1157	0.8731	0.037*
H7B	0.5982	−0.1486	0.8433	0.037*
C8	0.7895 (2)	0.0778 (2)	0.6596 (2)	0.0318 (4)
H8	0.8211	0.1176	0.7127	0.038*
C9	0.7547 (2)	0.0266 (2)	0.4916 (2)	0.0357 (5)
H9	0.7588	0.0248	0.4055	0.043*
C10	0.6817 (2)	−0.0505 (2)	0.5973 (2)	0.0344 (4)
H10	0.6266	−0.1132	0.5975	0.041*
C11	0.4496 (2)	0.46334 (19)	0.55623 (18)	0.0242 (4)
C12	0.4568 (2)	0.3221 (2)	0.5596 (2)	0.0327 (4)
H12	0.5256	0.2728	0.4897	0.039*
C13	0.3640 (2)	0.2543 (2)	0.6645 (2)	0.0326 (4)
H13	0.3716	0.1603	0.6641	0.039*
C14	0.2594 (2)	0.32470 (19)	0.77048 (18)	0.0261 (4)
C15	0.2498 (2)	0.4651 (2)	0.7673 (2)	0.0321 (4)
H15	0.1797	0.5143	0.8367	0.038*
C16	0.3426 (2)	0.5328 (2)	0.6629 (2)	0.0318 (4)
H16	0.3337	0.6270	0.6634	0.038*
C17	0.1584 (2)	0.2522 (2)	0.88668 (19)	0.0288 (4)
N1	1.10255 (19)	0.38726 (19)	0.32976 (17)	0.0341 (4)
N2	1.23205 (18)	0.53009 (17)	0.18881 (17)	0.0315 (4)
N3	0.82188 (19)	0.10780 (18)	0.53071 (16)	0.0323 (4)
N4	0.70506 (18)	−0.01762 (17)	0.70361 (15)	0.0286 (3)
O1	0.17403 (16)	0.12310 (14)	0.88583 (15)	0.0355 (3)
O2	0.06563 (18)	0.32386 (16)	0.97662 (15)	0.0418 (4)
O2W	0.08819 (17)	0.93824 (16)	0.11184 (15)	0.0354 (3)
O3W	0.64273 (19)	0.13798 (18)	0.20741 (18)	0.0471 (4)
O1W	0.91632 (17)	0.19506 (16)	0.20090 (14)	0.0353 (3)
H2A	0.128 (3)	0.984 (3)	0.040 (2)	0.053*
H2B	0.014 (2)	0.908 (3)	0.115 (3)	0.053*
H3A	0.715 (3)	0.175 (2)	0.202 (3)	0.053*
H3B	0.677 (3)	0.0563 (19)	0.180 (3)	0.053*
H1B	0.957 (3)	0.243 (2)	0.130 (2)	0.053*
H1A	0.958 (3)	0.1105 (17)	0.201 (3)	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03500 (10)	0.03866 (11)	0.03170 (10)	−0.01681 (7)	−0.00289 (7)	0.00291 (7)
C1	0.0356 (11)	0.0507 (13)	0.0313 (11)	−0.0134 (10)	−0.0098 (9)	−0.0015 (9)
C2	0.0344 (11)	0.0456 (12)	0.0412 (12)	−0.0159 (9)	−0.0118 (9)	−0.0049 (10)
C3	0.0277 (10)	0.0364 (11)	0.0306 (10)	−0.0102 (8)	−0.0044 (8)	−0.0021 (8)
C4	0.0315 (11)	0.0308 (11)	0.0403 (12)	−0.0079 (9)	−0.0050 (9)	0.0070 (9)
C5	0.0313 (14)	0.0285 (15)	0.0442 (15)	−0.0113 (10)	−0.0033 (11)	0.0055 (11)
C6	0.0295 (10)	0.0319 (10)	0.0240 (10)	−0.0112 (8)	−0.0062 (8)	0.0027 (8)
C7	0.0319 (10)	0.0327 (10)	0.0246 (9)	−0.0115 (8)	−0.0073 (8)	0.0056 (8)
C8	0.0316 (10)	0.0382 (11)	0.0260 (9)	−0.0151 (9)	−0.0069 (8)	0.0019 (8)
C9	0.0406 (12)	0.0438 (12)	0.0240 (10)	−0.0168 (10)	−0.0085 (8)	0.0003 (8)
C10	0.0391 (11)	0.0371 (11)	0.0292 (10)	−0.0153 (9)	−0.0101 (9)	−0.0008 (8)
C11	0.0232 (9)	0.0249 (9)	0.0243 (9)	−0.0071 (7)	−0.0078 (7)	0.0009 (7)
C12	0.0358 (11)	0.0256 (10)	0.0285 (10)	−0.0083 (8)	0.0004 (8)	−0.0030 (8)
C13	0.0384 (11)	0.0230 (9)	0.0322 (10)	−0.0106 (8)	−0.0050 (9)	−0.0003 (8)
C14	0.0241 (9)	0.0294 (10)	0.0258 (9)	−0.0093 (7)	−0.0094 (7)	0.0031 (7)
C15	0.0302 (10)	0.0300 (10)	0.0299 (10)	−0.0076 (8)	−0.0011 (8)	−0.0046 (8)
C16	0.0331 (10)	0.0228 (9)	0.0336 (10)	−0.0090 (8)	−0.0016 (8)	−0.0036 (8)
C17	0.0274 (9)	0.0318 (10)	0.0291 (10)	−0.0123 (8)	−0.0097 (8)	0.0017 (8)
N1	0.0312 (9)	0.0382 (10)	0.0312 (9)	−0.0133 (8)	−0.0053 (7)	−0.0005 (7)
N2	0.0249 (8)	0.0299 (9)	0.0352 (9)	−0.0075 (7)	−0.0049 (7)	−0.0002 (7)
N3	0.0327 (9)	0.0370 (9)	0.0256 (8)	−0.0137 (7)	−0.0062 (7)	0.0032 (7)
N4	0.0294 (8)	0.0310 (8)	0.0237 (8)	−0.0104 (7)	−0.0062 (6)	0.0020 (6)
O1	0.0360 (8)	0.0283 (7)	0.0378 (8)	−0.0146 (6)	−0.0038 (6)	0.0019 (6)
O2	0.0445 (9)	0.0343 (8)	0.0333 (8)	−0.0135 (7)	0.0052 (7)	−0.0010 (6)
O2W	0.0375 (8)	0.0371 (8)	0.0352 (8)	−0.0129 (6)	−0.0157 (7)	0.0029 (6)
O3W	0.0394 (9)	0.0453 (10)	0.0573 (10)	−0.0110 (8)	−0.0152 (8)	−0.0052 (8)
O1W	0.0397 (8)	0.0319 (8)	0.0295 (7)	−0.0129 (6)	−0.0030 (6)	−0.0007 (6)

Geometric parameters (Å, º) top

Ag1—N1	2.1209 (17)	C7—H7B	0.97
Ag1—N3	2.1237 (16)	C8—N3	1.326 (3)
Ag1—O1W	2.6611 (12)	C8—N4	1.344 (3)
C1—C2	1.350 (3)	C8—H8	0.93
C1—N1	1.378 (3)	C9—C10	1.355 (3)
C1—H1	0.93	C9—N3	1.372 (3)
C2—N2	1.371 (3)	C9—H9	0.93
C2—H2	0.93	C10—N4	1.368 (3)
C3—N1	1.328 (3)	C10—H10	0.93
C3—N2	1.338 (3)	C11—C16	1.399 (3)
C3—H3	0.93	C11—C12	1.400 (3)
C4—N2	1.469 (3)	C11—C11ⁱⁱⁱ	1.492 (4)
C4—C5	1.531 (3)	C12—C13	1.382 (3)
C4—C5A	1.564 (13)	C12—H12	0.93
C4—H4A	0.97	C13—C14	1.391 (3)
C4—H4B	0.97	C13—H13	0.93
C4—H4C	0.96	C14—C15	1.387 (3)
C4—H4D	0.96	C14—C17	1.509 (3)
C5—C5ⁱ	1.518 (5)	C15—C16	1.379 (3)
C5—H5A	0.97	C15—H15	0.93
C5—H5B	0.97	C16—H16	0.93
C5A—C5Aⁱ	1.49 (3)	C17—O2	1.251 (2)
C5A—H5C	0.97	C17—O1	1.269 (2)
C5A—H5D	0.97	O2W—H2A	0.857 (16)
C6—C7	1.519 (3)	O2W—H2B	0.842 (16)
C6—C6ⁱⁱ	1.531 (4)	O3W—H3A	0.865 (16)
C6—H6A	0.97	O3W—H3B	0.864 (16)
C6—H6B	0.97	O1W—H1B	0.863 (16)
C7—N4	1.473 (2)	O1W—H1A	0.842 (16)
C7—H7A	0.97

N1—Ag1—N3	169.34 (7)	N4—C7—H7B	109.1
C2—C1—N1	109.61 (19)	C6—C7—H7B	109.1
C2—C1—H1	125.2	H7A—C7—H7B	107.8
N1—C1—H1	125.2	N3—C8—N4	111.21 (18)
C1—C2—N2	106.38 (19)	N3—C8—H8	124.4
C1—C2—H2	126.8	N4—C8—H8	124.4
N2—C2—H2	126.8	C10—C9—N3	109.77 (18)
N1—C3—N2	111.13 (19)	C10—C9—H9	125.1
N1—C3—H3	124.4	N3—C9—H9	125.1
N2—C3—H3	124.4	C9—C10—N4	106.30 (18)
N2—C4—C5	112.46 (18)	C9—C10—H10	126.9
N2—C4—C5A	110.1 (5)	N4—C10—H10	126.9
N2—C4—H4A	109.1	C16—C11—C12	116.87 (17)
C5—C4—H4A	109.1	C16—C11—C11ⁱⁱⁱ	121.5 (2)
C5A—C4—H4A	136.1	C12—C11—C11ⁱⁱⁱ	121.6 (2)
N2—C4—H4B	109.1	C13—C12—C11	121.43 (18)
C5—C4—H4B	109.1	C13—C12—H12	119.3
C5A—C4—H4B	76.9	C11—C12—H12	119.3
H4A—C4—H4B	107.8	C12—C13—C14	120.93 (18)
N2—C4—H4C	109.8	C12—C13—H13	119.5
C5—C4—H4C	77.1	C14—C13—H13	119.5
C5A—C4—H4C	110.9	C15—C14—C13	118.11 (17)
H4B—C4—H4C	134.0	C15—C14—C17	120.18 (17)
N2—C4—H4D	109.4	C13—C14—C17	121.72 (17)
C5—C4—H4D	132.7	C16—C15—C14	121.05 (18)
C5A—C4—H4D	108.3	C16—C15—H15	119.5
H4A—C4—H4D	75.9	C14—C15—H15	119.5
H4C—C4—H4D	108.3	C15—C16—C11	121.60 (18)
C5ⁱ—C5—C4	112.6 (3)	C15—C16—H16	119.2
C5ⁱ—C5—H5A	109.1	C11—C16—H16	119.2
C4—C5—H5A	109.1	O2—C17—O1	124.92 (18)
C5ⁱ—C5—H5B	109.1	O2—C17—C14	117.50 (17)
C4—C5—H5B	109.1	O1—C17—C14	117.59 (17)
H5A—C5—H5B	107.8	C3—N1—C1	105.41 (17)
C5Aⁱ—C5A—C4	110.4 (13)	C3—N1—Ag1	127.40 (15)
C5Aⁱ—C5A—H5C	109.6	C1—N1—Ag1	127.18 (15)
C4—C5A—H5C	109.6	C3—N2—C2	107.47 (17)
C5Aⁱ—C5A—H5D	109.6	C3—N2—C4	125.54 (19)
C4—C5A—H5D	109.6	C2—N2—C4	126.99 (18)
H5C—C5A—H5D	108.1	C8—N3—C9	105.46 (17)
C7—C6—C6ⁱⁱ	111.4 (2)	C8—N3—Ag1	125.56 (14)
C7—C6—H6A	109.4	C9—N3—Ag1	128.95 (14)
C6ⁱⁱ—C6—H6A	109.4	C8—N4—C10	107.26 (16)
C7—C6—H6B	109.4	C8—N4—C7	126.55 (17)
C6ⁱⁱ—C6—H6B	109.4	C10—N4—C7	126.19 (17)
H6A—C6—H6B	108.0	H2A—O2W—H2B	116 (2)
N4—C7—C6	112.45 (16)	H3A—O3W—H3B	111 (2)
N4—C7—H7A	109.1	H1B—O1W—H1A	114 (2)
C6—C7—H7A	109.1

N1—C1—C2—N2	−0.1 (3)	C2—C1—N1—Ag1	−178.88 (15)
N2—C4—C5—C5ⁱ	61.3 (4)	N3—Ag1—N1—C3	177.4 (3)
C5A—C4—C5—C5ⁱ	−32.3 (8)	N3—Ag1—N1—C1	−3.9 (5)
N2—C4—C5A—C5Aⁱ	−68.5 (14)	N1—C3—N2—C2	−0.1 (2)
C5—C4—C5A—C5Aⁱ	32.3 (9)	N1—C3—N2—C4	179.42 (18)
C6ⁱⁱ—C6—C7—N4	173.50 (19)	C1—C2—N2—C3	0.1 (2)
N3—C9—C10—N4	−0.6 (3)	C1—C2—N2—C4	−179.36 (19)
C16—C11—C12—C13	−1.0 (3)	C5—C4—N2—C3	−121.4 (2)
C11ⁱⁱⁱ—C11—C12—C13	179.5 (2)	C5A—C4—N2—C3	−82.8 (6)
C11—C12—C13—C14	0.2 (3)	C5—C4—N2—C2	58.1 (3)
C12—C13—C14—C15	0.7 (3)	C5A—C4—N2—C2	96.6 (6)
C12—C13—C14—C17	−179.23 (19)	N4—C8—N3—C9	−0.2 (2)
C13—C14—C15—C16	−0.8 (3)	N4—C8—N3—Ag1	−178.33 (13)
C17—C14—C15—C16	179.08 (19)	C10—C9—N3—C8	0.5 (3)
C14—C15—C16—C11	0.1 (3)	C10—C9—N3—Ag1	178.52 (15)
C12—C11—C16—C15	0.8 (3)	N1—Ag1—N3—C8	12.2 (5)
C11ⁱⁱⁱ—C11—C16—C15	−179.6 (2)	N1—Ag1—N3—C9	−165.4 (3)
C15—C14—C17—O2	1.4 (3)	N3—C8—N4—C10	−0.1 (2)
C13—C14—C17—O2	−178.69 (19)	N3—C8—N4—C7	−179.62 (18)
C15—C14—C17—O1	−178.55 (18)	C9—C10—N4—C8	0.4 (2)
C13—C14—C17—O1	1.3 (3)	C9—C10—N4—C7	179.93 (19)
N2—C3—N1—C1	0.0 (2)	C6—C7—N4—C8	64.4 (3)
N2—C3—N1—Ag1	178.97 (13)	C6—C7—N4—C10	−115.0 (2)
C2—C1—N1—C3	0.1 (3)

Symmetry codes: (i) −x+3, −y+1, −z; (ii) −x+1, −y, −z+2; (iii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O1^iv	0.86 (2)	1.99 (2)	2.833 (2)	166 (3)
O2W—H2B···O1^v	0.84 (2)	1.95 (2)	2.779 (2)	169 (3)
O3W—H3B···O1^vi	0.86 (2)	2.05 (2)	2.877 (2)	160 (2)
O3W—H3A···O1W	0.86 (2)	2.02 (2)	2.852 (2)	161 (2)
O1W—H1A···O2W^vii	0.84 (2)	2.03 (2)	2.802 (2)	153 (2)

Symmetry codes: (iv) x, y+1, z−1; (v) −x, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₁₄N₄)(H₂O)](C₁₄H₈O₄)_0.5·2H₂O
M_r	472.27
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.7685 (6), 10.0659 (6), 10.9224 (7)
α, β, γ (°)	80.190 (1), 68.898 (1), 74.775 (1)
V (Å³)	963.36 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.23 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.81, 0.86
No. of measured, independent and observed [I > 2σ(I)] reflections	5289, 3569, 3422
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.058, 1.06
No. of reflections	3569
No. of parameters	267
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.42

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N1	2.1209 (17)	Ag1—O1W	2.6611 (12)
Ag1—N3	2.1237 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O1ⁱ	0.86 (2)	1.99 (2)	2.833 (2)	166 (3)
O2W—H2B···O1ⁱⁱ	0.84 (2)	1.95 (2)	2.779 (2)	169 (3)
O3W—H3B···O1ⁱⁱⁱ	0.86 (2)	2.05 (2)	2.877 (2)	160 (2)
O3W—H3A···O1W	0.86 (2)	2.02 (2)	2.852 (2)	161 (2)
O1W—H1A···O2W^iv	0.84 (2)	2.03 (2)	2.802 (2)	153 (2)

Symmetry codes: (i) x, y+1, z−1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x+1, y−1, z.

Acknowledgements

The author thanks Baicheng Normal College for supporting this work.

References

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